361593

Sigma-Aldrich

Artemisinin

98%

Synonym(s):
Qinghaosu, Arteannuin
Empirical Formula (Hill Notation):
C15H22O5
CAS Number:
Molecular Weight:
282.33
MDL number:
PubChem Substance ID:
NACRES:
NA.79

Quality Level

assay

98%

optical activity

[α]20/D +76°, c = 0.5 in methanol

mp

156-157 °C (lit.)

Mode of action

enzyme | inhibits

antibiotic activity spectrum

parasites
viruses

SMILES string

C[C@@H]1CC[C@H]2[C@@H](C)C(=O)O[C@@H]3OC4(C)CC[C@@H]1[C@@]23OO4

InChI

1S/C15H22O5/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-20-15/h8-11,13H,4-7H2,1-3H3/t8-,9-,10+,11+,13-,14-,15-/m1/s1

InChI key

BLUAFEHZUWYNDE-NNWCWBAJSA-N

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General description

Artemisinin is extracted from sweet wormwood (Artemisia annua). It has anticancer, antiprotozoal and antiviral activities. Artemisinin is associated with brainstem encephalopathy.

Application

Artemisinin has been used:
  • in drug susceptibility assays
  • as a standard for its quantification from artemisinin from hairy roots
  • to check cell viability using 3-(4, 5-dimethylthiazol-2yl)-2,5-diphenyl tetrazolium bromide (MTT) assay
  • as an antimalarial agent to investigate the role of autophagy-related (ATG) genes throughout the P. falciparum asexual and sexual blood stages

Packaging

100 mg in glass bottle

Biochem/physiol Actions

Artemisinin (Qinghaosu), a sesquiterpene lactone, is a highly active anti-malarial (falciparum malaria) drug. Artemisinin is also an anthelmintic (parasitic worm) effective against the blood fluke, schistosomiasis.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 361593.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

storage_class_code

11 - Combustible Solids

WGK Germany

WGK 3

Flash Point F

Not applicable

Flash Point C

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

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  4. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  5. In what solvents is Product 361593, Artemisinin, soluble?

    According to the chemicals encyclopedia published by the Royal Society of Chemistry, artemisinin is expected to be soluble in most aprotic solvents and slightly soluble in oil. Sigma-Aldrich tests the solubility of this product in chloroform at 25 mg/mL. Our quality control is also able to prepare a 0.5% solution in methanol in order to measure the optical rotation.

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    Ask a Scientist here.

Rita Piedade et al.
Expert opinion on drug metabolism & toxicology, 7(10), 1185-1200 (2011-09-09)
Plasmodium falciparum malaria is one of the world's most lethal infectious diseases, commanding millions of drug administrations per year. The pharmacogenetics of these drugs is poorly known, although its application can be pivotal for the optimized management of this disease....
Antiprotozoal drugs
Simooya OO
Side Effects of Drugs Annual, 30, 336-342 (2008)
Deciphering genetic regulation of CD14 by SP1 through characterization of peripheral blood mononuclear transcriptome of P. faiciparum and P. vivax infected malaria patients
Chakraborty B, et al.
EBioMedicine, 37, 442-452 (2018)
Jürg Utzinger et al.
Current opinion in investigational drugs (London, England : 2000), 8(2), 105-116 (2007-03-03)
Schistosomiasis is a significant health issue caused by a blood fluke that affects more than 200 million individuals worldwide, over half of whom suffer from disease-associated symptoms. In areas of high burden, disease is mainly managed by controlling morbidity with...
Pierre-Eric Campos et al.
Marine drugs, 17(3) (2019-03-17)
Chemical study of the CH₂Cl₂-MeOH (1:1) extract of the sponge Fascaplysinopsis reticulata collected in Mayotte highlighted three new tryptophan derived alkaloids, 6,6'-bis-(debromo)-gelliusine F (1), 6-bromo-8,1'-dihydro-isoplysin A (2) and 5,6-dibromo-8,1'-dihydro-isoplysin A (3), along with the synthetically known 8-oxo-tryptamine (4) and the...

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